The Confidence Game: Why Great Leaders Doubt Themselves--Encore Presentation

What does a person’s behavior suggest about their level of competence?

Popular culture and other pressures distort our views of leadership and competence. Recently I wrote about the myth surrounding the “heroic leader.” Related to that myth is the myth of competence and the hyper-confident leader.

Many of the stories we love involve heroes who not only display supernatural competence but also act with preternatural confidence. I’m thinking of Sherlock Holmes, Cordelia Cupp, or any number of those super-spy characters: James Bond, Ethan Hunt, and their ilk. We thrill at the protagonist eagerly pursuing and resolving mystery after mystery and crisis after crisis, each of which would render ordinary mortals catatonic with indecision and even fear.

In contrast, many of our favorite comedies involve doofuses who have no idea of their supreme ineptitude yet proceed through life with the same confidence as the super-spy. It’s the Dunning-Kruger effect played for laughs. I’m thinking of Dumb and Dumber, the Pink Panther, or even some of Shakespeare’s comedic characters, such as the “mechanicals” in Midsummer Night’s Dream. A classic example is Seinfeld’s Elaine Benes unabashedly breaking out the most cringeworthy dance moves in front of her coworkers.

So much for fiction. Meanwhile in reality-land, where we dwell, things look quite different and incompetence and the havoc it wreaks rarely warrant a chuckle.

The most competent among us aren’t hyper-confident and are often riven with self-doubt, which you might not realize if you aren’t close to them or you actually are them. I’m not talking about imposter syndrome. The self-doubt a competent leader experiences is an entirely healthy and even necessary element of their competence.

Think about it logically. To be competent, you must take into consideration all aspects of a problem, including what can go wrong. You also know that no one is perfect. Therefore, the competent leader questions their own ability and anticipates and even prepares for error and failure.

At the same time, the most incompetent, since they don’t really understand or care about the issues they face and generally lack self-awareness, are convinced of their invincibility. This is dark side of Dunning-Kruger. Think of the politician who makes bold proclamations that never seem to manifest yet continues to boast about what they will do “someday”—just you wait! It takes a superhuman amount of chutzpah to spout a steady stream of such BS in public.

It would be the stuff of comedy if the stakes weren’t so damn high.

What’s at work is a bit of a paradox. The most competent people have the confidence to feel self-doubt. Meanwhile, the most seemingly confident lack the self-assurance to doubt themselves and are likely altogether incompetent. Got that?

Nonetheless, we often assume self-doubt to be inherently debilitating. It’s true that if you have overwhelming or misdirected self-doubt, it can overtake your will. It won’t matter if you’re genuinely competent or not; chronic self-doubt will render you ineffective. Self-doubt that hinders progress is unhealthy.

But self-doubt doled out in rational doses constitutes a vital component of competence. Competent people doubt themselves because they neither assume nor pursue impossible perfection.

Plus, every complex decision has multiple dimensions, from the logistical (How should we do this and when?) to the ethical (Why should we do this?) to the epistemological (How do we know we’re seeing this clearly and fully?).

Anyone claiming the mantle of leadership and not considering versions of these questions with every decision is not much of a leader. Say it with me: they’re a boss!

I will go further. The person who is supremely confident at all times, who rarely hesitates and always claims to know precisely what to do, who never expresses concerns or betrays misgivings, who always seems to have it all together, who never misses a beat, and so on—well, there are two possibilities with regard to that person:

1. They really are competent and, from a distance, they seem confident. Up close is a different story, though: they are rationally self-doubting.

2. They’re simply incompetent.

How do you tell the difference? Look to their track record. How well do they perform over the long term? A run of avoidable failures points to incompetence. Another tell-tale sign is that the incompetent tend to ignore, dismiss, deflect, or altogether deny their screwups. If we applied this analysis to our political leaders, how would that affect our voting?

The longtime CFO at a college I served as a vice president was one of these hyper-confident types. He would sit in meetings and rattle off facts and figures from the top of his head like he had everything memorized. No one seemed concerned when he didn’t back up his numbers.

The president adored him, admired his self-assuredness, and rarely questioned any of his public pronouncements. It also helped that his numbers magically seemed to support her wants.

I had a different perspective. When I first took the VP job, I received no budget numbers from him at all. Naturally, I paid the CFO a little visit and after a few niceties asked him point blank what my actual budget was. He replied, “We’ll figure it out,” and added with a puckish grin, “Just don’t overspend it.”

Despite his facetious tone, I took his joke as a serious warning. Subsequently, I made several attempts to learn what money I had available to no avail. The president was no help and waved off my concerns. So, I was in the treacherous position of having to spend budgetary money without any clue as to how much was available let alone how it was allocated. (Frighteningly, this was not my first experience with this situation.)

I should point out that this college had limited resources and a soul-crushing scarcity mentality. Meanwhile, I had little trouble identifying areas of waste, some overseen by the budget office. It became difficult to discern whether the CFO’s cockiness was genuine obliviousness or just another confidence game.

The president relied on and trusted the CFO without question, so when the CFO suddenly died, she was naturally devastated. His newly-hired number-two had to take over in an emergency acting capacity.

Now, here at last was someone I could deal with. He was forthright and humble—the president would say to a fault. She was used to years of listening to BS delivered with brash self-assurance, and now here was a guy who said, “I don’t know,” when he didn’t know.

Turns out that many of those numbers the old CFO would rattle off were never written down. The new acting CFO had little to work with and spent most of his time reconstructing what should already have existed while fending off the auditors, the president, and budgetary disaster.

According to the president, who complained to me privately, she missed the old CFO’s bold self-assurance and resented the acting CFO’s seeming uncertainty. Of course to my mind, she had it entirely backward, which is not surprising. Just like her beloved late CFO, she never doubted her own competence even as the college sank lower and lower on her watch. I was witnessing the Dunning-Kruger effect in real time.

In the end, how did the president reward the acting CFO for heroically stepping up to take over in a crisis and telling the unvarnished truth about the budget? Predictably, she hired a permanent CFO and unceremoniously busted the acting CFO back to a supporting role.

The whole thing would have made a hilarious episode of The Office, but there were no laughs to be had in reality.

By the way, I never did learn my budget amount though I carefully avoided overspending it.

My point is rather simple. The appearance of confidence doesn’t correlate with actual competence, and extreme confidence may be a tell-tale sign of incompetence. Hyper-confidence is an illusion—either a self-deception or a con.

Which is not to say that self-doubt itself is a sign of competence any more than it demonstrates incompetence. It’s a matter of degree.

As with the hyper-competent detective or super-spy, hyper-confident competence is fiction. Real competence requires doubt. True leaders paradoxically have the confidence to embrace and even express that doubt. Otherwise, they know, their decisions can never be trusted.

So, if you want to be a competent leader, truly competent, allow yourself to experience healthy doubt. Question yourself, your motivations, your information, your biases, and so on. But don’t let indecision hamper you or morph into some version of analysis paralysis. It’s a careful balance. And never forget that the most supremely confident, the ones who strut and boast and never show fear, are frauds.

True competence requires self-awareness and healthy self-doubt, not phony hyper-confidence.

Still there?

Then you must be pretty tired of the predictable platitudes the leadership advice-industrial complex doles out if you’re still here.

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